Opening of School

A view of the front of Cluett Hall at Trinity-Pawling School

Preparing for the 2023-2024 School Year

Students and parents, we are looking forward to welcoming you to campus this fall!

This page will serve as the central location for all information relevant to the opening of school, for new and returning students and families. Please be sure to review the information carefully under each tab below to complete your Back to School Checklist. Also, please continually check this page for updates as information is added throughout the summer months. Roll Pride!

Updated August 29, 2023

Frequently asked Questions

While the start of a new school year comes with great excitement, we also recognize that it can come with many questions. To ensure that your sons are fully prepared for their time at Trinity-Pawling, please visit our Opening of School FAQs page to find your answers!

View Opening of School FAQs

School Calendar

Saturday, September 2
Early Sports Arrival
(New and Returning Boarding / New and Returning Day Students who are playing a fall varsity sport)

Friday, September 8
All Remaining New and Returning Boarding Students (Grades 9-PG), New and Returning Day Students (Grades 9-PG), and Middle School Boarding Students Arrive

Saturday, September 9
Middle School Day Students (Grades 7-8) Arrive and participate in Middle School Orientation

Friday-Sunday, September 8-10
Student Orientation Activities for all Students

Monday, September 11
Fall Term Classes Begin

View Full Opening of School Schedule

Parent Directory

Stay connected with other Pride Parents! Be sure to view the secure Parent Directory for the 2023-2024 school year in the Parent Portal.

Parent Directory

A view of the new brick walkway around the quad at Trinity-Pawling
Save the Date!
Parents' Weekend 2023

Mark your calendars, Pride Parents! Parents' Weekend 2023 will be held on campus on October 20-21, 2023. Please stay tuned for more information.

Required Summer Reading 2023

Buy Textbooks

New Students:
Submit ID Photo

Community Handbook

Updated June 2023

View Handbook